ABS Plastic compositions containing bio-aryloxy flame retardants

ABSTRACT

Plastic compositions containing acrylonitrile-butadiene-styrene and bis-aryloxy compounds having the formula   WHEREIN ARYL IS FROM THE GROUP   Z is bromine or chlorine, m and m&#39;&#39; are integers having a value of 1-7, y is an integer having a value of 1-5, i and i&#39;&#39; are integers having a value of 0-2, and A is cyano, nitro, lower alkoxy, lower alkyl, fluorine, dialkylamino, phenyl, halo-phenyl, benzyl or halo- benzyl and alkylene is a straight or branched chain alkylene group having from 1 to 6 carbon atoms.

United States Patent [1 1 Anderson et al.

[4 1 July 15,1975

[ ABS PLASTIC COMPOSITIONS CONTAINING BIO-ARYLOXY FLAME RETARDANTS [75]Inventors: Arnold L. Anderson; Robert J.

Nulph, both of Alma, Mich.

[73] Assignee: Michigan Chemical Corporation, St. Louis, Mich.

[22] Filed: Feb. 8, 1973 [21] Appl. No.: 330,801

Related U.S. Application Data [63] Continuation-impart of Ser. No.260,240, June 6, 1972, abandoned.

[52] U.S. Cl 260/459 R; 260/42; 260/4222; 260/4575 R [51] Int. Cl. C08f45/60 [58] Field of Search 260/459 R, 45.95 G, 613 B, 260/332 R, 2.5 A1,DIG. 24; 106/15 FP [56] References Cited UNITED STATES PATENTS 3,658,6344/1972 Yanagi et a1 161/403 3,717,609 2/1973 Kutner 260/4595 G PrimaryExaminerM. J. Welsh Attorney, Agent, or FirmR0bert M Phipps; James J.Mullen; Robert S. Frieman [5 7] ABSTRACT Plastic compositions containingacrylonitrilebutadiene-styrene and bis-aryloxy compounds having theformula 18 Claims, No Drawings 1* ABS PLASTIC COMPOSITIONS" CONTAININGBlO-ARYLOXY FLAME RETARDANTS This applicationis a continuation-impart ofcopending applicatiQn-SerQNo. 260,240,. -filed '.lune 19,72 and nowabandoned. The entire specification of this case; SerfNo 2,60',2,40, isto be considered as incorporated herein byreference: 1" a A The priorart consii ered in conjunction with the preparatiomof-this applicationis asfollows: US. Pat. No. 2,130,9905 US. Pat. No. 2,186,367; US Pat.No. 2,329,033; Us. Pat. NO. 3,666,692; ,Us. Pin No. 3,686,320; -U.SPa.t.' No. 3,658,634; German Pat. No. 1,139,636; German Pat. No,2,054,522} Japanese Pat. No. (72) 14,500 as cited in Volume 77, ChemicalAbstracts, column l53737k (1972); Chemical Abstracts, Volume 13, column448 Chemical Abstracts, Volume 31, column 7045 and Journal of theChemical Society, pages 297 22 976 1963). All of these publications areto be considered as'incorporated herein by reference.' j

The presentinvention relates to plastic compositions containingacrylonitrile-butadiene-styrene (herein referred to as ABS). Morespecifically, the present invention covers plastic compositionscontaining ABS and certain bis-aryloxy compounds (hereinafter defined).as flame retardants for, said plastic compositions. I

ABS plastics and utility thereof are known in the art.

as exemplified: ABS Plastics, C. H. Basdekis', (Rei nhold PlasticsApplications Series), Reinholdipublishing Corporation,-New York, 1964andModern Plastics Encyclopedia 1972-1973 Vol. 49: No. 10A, October,1972, pages 10, 14, l6, l7, 19 142 and 143 and which publications are intoto incorporated herein by reference. 1" A The need forflarheiretardinggABS plastics has also been recognized in the art aszexemplified by US. Pat.

N6. 3,422,048f*and u.s. Pa'L'No, 3,418,263 and Modern PlasticsEncyclopedia, ibid, pages 142, 143, 202, 203 and 456+f458 and whichpublications are in totoincorporated herein by reference.

The resultantclisadvantages in the utilization-of various prior art materials as flame retardants for ABStinclude, withoutilimitation, factorssuch as thermal migration, heat, instability, light instabilitynonbiodegradable toxicity, discoloration and the large amountsemplo'ye'd in order to be' effective. Thus, there is always a demand fora material which will function as a flame retardant in ABS andconcurrently will not, by incorporation therein, adversely effect thechemical and/or physical and/or mechanical properties of the resultantABS plastic composition.

The prior art pr'oblern of providing a flame retarded ABS compositionhaving desired chemical, physical and mechanical properties has now beensubstantially solved by the present invention and the abovedescribeddisadvantages substantially overcome.

Accordingly, one of the main objects of the present invention is toprovide ABS plastic compositions which are flame retarded:

Another object of the pisent'in'vention is toprovide a material for ABS-plastic compositionswhich'will not substantiallyadversely effect thechemical and/or physical and/or mechanical properties of saidcompositions.

A furthe'robject of the present invention is to provide a flameretardant which is economic and easy to incorporate into ABS plasticswithout being degraded orde- 2', composed as a r'es'ult 'of ble'ndin'gbrprocessing operations v "It Has been found th at the ffor'ego'in'gobjects 'can be obtair'i'ed-b'y the incorporation of a new class of bis-5' aryloxy compounds in ABS to subsequently provide flame retardedcompositions which exhibit outstanding chemical, physical and mechanicalproperties.

The bis-aryloxy compounds used in the present invention compositionshave the formula: l0

In Formula liabove, aryl is from the group Z is bromine or chlorine; inand m are integers each independently having'a value of 1-7; i and i areintegers each independently having a value of 0-2; alkylene is astraightor branched chain alkylene group having from 1 to 6 carbon atomse.g. CH C H,, C H C l-l C H C H and CH CH(CH )CH A is from the groupcyano. (C N), nitro (NO lower alkoxy (eigt' OCH lower--alkyle.g. CH C HC l-l Cflr'l fluorine, dialkylamino e.g. N (CH -N(C H i-,.-)' ,Q;phenyl(C H halo-phenyl', benzyl (C H C H,=,'),iand halo-benzyl; and y is aninteger having a value 20f; 1 -65.

the sum ofi+m or i m is not greater than 7 ands is not greater than 5.

It is'to be understood that all of'the compounds falling withiii theabove Formual land as heretofore del l l I l l Compound tllkylene 4 h 44 4 4 HI H6 H H4 4 -l 4 C1H CH1.

0 (alkylene) 0 (aryl) Table I fined are generically described herein asbis-aryloxy" compounds.

Illustrative (but without limitation) of some of the present inventionbis-aryloxy compounds are shown below:

the exemplary definitions of A, Z alkylene, aryl, m, m i, i and y arelisted in Table I.

where aryl ound N0. Z In Cl 2 Br 3 Br 2 Br 2 Br 3 Br 2 Cl 2 Br 2 Br 2 ClSl 52 51 l 54 55 56 57 58 59 60 6| 62 63 64 65 66 67 68 69 70 7| 72 73 OCH(CH3)CH2CH2 2 CH CH(CH 1)CH CH l l i' ulkylcne Com- Com pound No.

O O 0 l l l l l 0 O (l l l l l 1 -OCH3 m 73522237 2 mmmmmmmm d W 6789023 0N 77777888 p O 5 6 6 M r. H mtmmmmmmtmn .llll 2|. 2r. fxwmxmx hwHHHCHH(HHH( mmmmmm kwwm k kfwirxm HHHHHHWHHH CCCCCC(CCC( :HH 1 C 5 N0 H("m CNMMC NC F In general, the bis-aryloxy compounds are prepared byreacting a halogenated naphthol with a halogenated alkane or amonohalophenoxy haloalkane (depending upon which bis-aryloxy compound isdesired) at elevated temperatures in the presence of a basic materialsuch as alkali metal hydroxides, carbonates, bicarbonates, oxides andhydrides, The preferred alkali metals are potassium and sodium. Whereone desires to increase, for example, ease of handling the reactionmass, solvents such as ketones (e.g. acetone, methyl ethyl ketone, andmethyl iso-butyl ketone), alcohols (e.g. methanol, ethanol, iso-propylalcohol, butyl alcohol and glycols), or aqueous solvents (e.g. water, amixture of water and alcohol and a mixture of water and ketone) can beemployed. The desired end product, i.e. the bis-aryloxycompound, can berecovered from the reaction mass via various methods such asdistillation or crystalization after cooling the reaction mass to about1030C and adding water thereto, Where the 'end product requires recoveryvia crystallization, various aromatic solvents such as benzene, toluene,xylene, dichlorobenzene and the like can be used.

Specifically, the bis-naphthoxy compounds are 'pre-- pared according tothe following reactions:

In the above reaction, X is halogen, preferably chlorine and alkylene isthe same as defined herein. Where m and m and i and i are differentintegers, then equivalent molar portions of the particular halogenatednaphthol are used with equivalent portions of dissimilar halogenatednaphthol.

Specifically, the unsymmetrial aryloxy compounds are prepared, forexample, according to the following reactions:

031+ base (e.g.NaOH 5 A. (It) Zn A1 0 ONa X(a1kylene) 0 Z A Y A r Z15%\-0(alky1ene) 0- Z In the above reaction, X is halogen, preferablychlorine, and alkylene is the same as defined herein.

The above reactions are conducted at temperatures ranging from thefreezing point of the initial reaction mass to the boiling pointthereof. Preferably the temperatures are from about C to about 200 C andmore preferably from about 50 C to about 175 C. It is to be understoodthat the reaction can be conducted under sub-atmospheric (e.g. 1/10-8/10atmospheres), atmospheric or super-atmosphere (e.g. l.5lO atmospheres)pressure. Preferably, the reaction is carried out at atmosphericpressure.

The above-described processes can be carried out with conventional,readily available chemical processing equipment. For example, aconventional glass-lined vessel provided with heat transfer means, areflux condenser and a mechanical stirrer can be advantageously utilizedin practicing any of the preferred embodiments of the inventiondescribed in the examples set forth herein.

The'arn'ount of bis-aryloxy compound employed in the present inventioncompositions is any quantity which will effectively render theacrylonitrilebutadiene-styrene containing composition flame retardant.In general, the amount used is from about 1% to 25% by weight, based onthe total weight of the composition. Preferably, the amount employed isfrom about 5% to about 20% by weight. It is to be understood that anyamount can be used as long as it does not substantially adversely effectthe chemical and/or physical and/or mechanical properties of the endpolymer composition. The amount utilized, however, is such amount whichachieves the objectives described herein.

It is to be understood that the term ABS as used herein meansacrylonitrile-butadiene-styrene copolymers which are thermoplasticpolymers produced, for example (but without limitation), by blending astyrene/acrylonitrile copolymer with butadiene-based rubber, or bygrafting butadiene-based rubber (usually polybutadiene) withstyrene/acrylonitrile chains, or by copolymerization of styrene,acrylonitrile and butadiene monomers.

Thus the acrylonitrile-butadiene-styrene used in the present inventioncompositions is any acrylonitrilebutadiene-styrene herein defined andwhich one so desires to flame retardj It is to be understood that theacrylonitrilerbutadien'e-styrene used can be a virgin material, i.e.substantially free of additives such as stabilizers, plasticizers; dyes,pigments, fillers, and the like, or the acrylonitrile-butadiene-styrenecan have additives (such as those mentioned and described herein)already contained therein or added concurrently with or after theaddition of the bis-aryloxy compounds.

Another facet of the present invention relates to the use of certainmetal compounds with the bis-aryloxy compounds to promote a cooperativeeffect therebetweenand thus enhance the flame retardancy of theresultant plastic composition as compared to the flame retardancy ofeither one component used separately. These enhancing agents are fromthe group antimony, arsenic, bismuth, tin and zinc-containing compounds.Without limitation, examples of said enhancing agents include Sb O SbClSbBr SbI SbOCl,

AS AS 05, Z1180. BaB O .H O, 2.ZnO.3BgO3-3.5-

H 0 and stannous oxide hydrate. The preferred enhancing agent isantimony trioxide.

The amount of enhancing agent employed in the present inventioncompositions is any amount which when used with said bis-aryloxycompounds will promote a cooperative effect therebetween ln general, theamount employed is from about 1% to about pref erably from about 2% toabout 10%, by weight, based on, the total weight of plastic composition.Higher amounts can be used as long as the desired end result isachieved. v i ltis also within the scope of the present invention toemploy other materials in the present invention compositions whereone sodesires to achieve a particularend result. Such materials include,withoutlimitation, adhesion promotors; antioxidants; antistatic agents;antimicrobials; ,colorants; flame retardants such as those listed onpages 456458, Modern Plastics Encyclopedia, ibid, (in addition to thenew class of flame retardants described herein); heat stabilizers; lightstabilizers; pigments; plasticizers; preservatives; ultravioletstabilizers and fillers.

lnthis latter category, i.e. fillers, there can be mentioned withoutlimitation, materials such as glass; carbon; cellulosic fillers (woodflour, cork and shell flour); calcium carbonate (chalk, limestone, andprecipitated calciumcarbonate); metal flakes; metallic oxides (aluminum,beryllium oxide and magnesia); metallic powders (aluminurn, bronze,lead, stainless steel and zinc); polymers (comminuted polymers andelastomer-plastic blends); silica products (diatomaceous earth,novaculite, quartz, sand, tripoli, fumed colloidal silica, silicaaerogel, wet process silica); silicates (asbestos, kaolimite, mica,nepheline syenite, talc, wollastonite, aluminum silicate andcalciumsilicate); and inorganic compounds such as barium ferrite, bariumsulfate, molybdenum disulfide and silicon carbide. I I

The above mentioned materials, including fillers are more fullydescribed in Modern PlasticsEricyclopedia, ibid, and which publicationis incorporated herein in toto). by reference.

The amount of the above described materials employed in the presentinvention compositions can be any quantity which will not substantiallyadversely effect the desired results derived from the present inventioncompositions. Thus, the amount used can be zero (0) percent, based onthe total weight of the composition, up to that percent at which thecomposition can still be classified as a plastic. ln general, suchamount will be from about 0% to about 75% and specifically from about 1%to about 50%; i

Thebis-a ryloxy compounds can be incorporated in to theacrylonitrile-butadiene-styrene at any processing stage in 'order, toprepare the present invention compositions In general, this isundertaken prior: to fabrication either by physical blending or duringthe process of forming acrylonitrile-butadiene-styrene per se. Where oneso desires, the bis-aryloxy compounds may be micronized: into finelydivided particles prior to incorporation into theacrylonitrile-butadiene-styrene.

EXAMPLE 1 An ABS plastic material, (Marbon TIE-2098, a product of.Marbon Division, BorgEWarner Corporation,

plastic by adding both to a Brabender mixer (Plastic- Corder, TorqueRheometer, Model PLV-lSO, C. W. Brabender lnstrumentslnc., SouthHackensack, N.. l.). The mixer is equipped witha pair of roller typeblades positioned within a head provided withheat transfer means- Theresultant mixture .is heated to about 245 C.; at

this temperature, it is in a molten state. The percentages by weight ofeach component utilized in the respective formulations are listed inTablell. Each for l mulation is discharged from the mixer and uponcooling solidifies and is ground into chips. The chips are subjected tocompression molding in a Wabash press by placing said chips between twoplatens, the bottom of which contains four equal size depressions threeinches by five inches by one/eighth inch deep. The top platen is thenplaced over the bottom platen and heat transfer means supplied theretoin order to melt said chips and thus provide solid samples (aftercooling) for testing. Portions of the solid samples off each respectiveformulation (Nos. l26) prepared according to the'above describedprocedure are than subjected to two different standard flammabilitytests, i.e. UL 94 and ASTM D-2863-70. The UL 94 is, in general, theapplication of a burner to a test speciment (strip) for a certain periodof time and observation of combustion, burning, and extinguishment. Thisprocedure is fully set forth in Underwriters Laboratories bulletinentitled UL 94, Standard for Safety, First Edition, September 1972 andwhich is incorporated herein by reference. ASTM No. D-2863- is aflammability test which correlates the flammability of a plasticspecimen to the available oxygen in its immediate environment; thiscorrelation is stated as an Oxygen Index, 0.1., level predicated uponthe percent oxygen in the gaseous medium which is required to justprovide a steady state of continuous burningof the plastic specimen.This ASTM method is.

fully described in 1971 Annual Book of ASTM Standards Part 27, publishedby the American Society For Testing and Materials, 1916 Race Street,Philadelphia, Pa.: this publication is to be considered as incorporated(in toto) herein by reference.

The results of these flammability tests are shown in Table II.

Table II FLAMMABILITY DATA FOR ABS PLASTIC COMPOSITIONS CONTAININGBIS-ARYLOXY COMPOUNDS FORMULA- BlS-ARYLOXY COM- ENHANCING OXYGEN UL TIONPOUND AGENT INDEX NO. NO. 7c Sb O 7? 94 l. O I85 SB 2. 2 l 0 22.0 SB 3.2 l5 5 31.5 SE 0 4. 5 l5 0 21.5 SB 5. 5 l5 5 29.5 SE-O 6. l5 l5 0 20.5SB 7. l5 l5 5 28.0 SE-l 8. 27 0 22.0 SB 9. 27 I5 5 30.0 SE-O I0. 33 l5 021.0 SB 1 l. 33 I5 5 29.0 SE-0 I2. 40 l5 0 215 SB I3. 40 I5 5 28.5 SE-]14. 53 I5 0 21.5 SB 15. 53 I5 5 29.5 SE-O I6. 58 I5 0 20.5 SB 17. 58 I55 28.5 SE-l I8. 65 I5 0 2| .0 SB 19. 65 I5 5 28.0 SE-l 20. 73 l5 0 22.5SB 21. 73 I5 5 29.5 SE-O 22. 77 I5 0 22.0 SB 23. 77 I5 5 30.5 SE4) 24.83 I 5 0 21.0 SB 25. 83 I5 5 9.5 SE-0 26. 91 I5 5 0 SE-0 Referring toTable II, the bis-aryloxy compound number relates to the structuralformulae heretofor set forth in Table I; a difference of 2% in theOxygen Index values is considered significant; and the UL 94 values (I)i g s ig ASTM Test Nu D6386: are on a graduated scale wherein thehighest degree to (3) nexuwl Strength ASTM Test N0v 7904 lowest degreeof flame retardancy is respectively SE-O, g f i v g t ggm 2 E 31:22-22;and SE-l, SE-Z, SB and Burns. 2 3; 5, g, The results shown in Table IIdemonstrate the unique Temperature (HDT) ASTM Test No. D648-56.effectiveness of these bis-aryloxy compounds as flame retardants forABS, Specifically, formulation No. 1 Each of the aforementioned ASTMTests are stan- (the control) had a 0.1. of 18.5 and UL 94 value of SB.dard tests in the art and are utilized collectively in In Nos. 2, 4, 6,8, 10, 12, 14, 16, 18, 20, 22 and 24, the order to ascertain theefficacy ofa polymeric system as se of h particular bis-aryloxy compoundresults in a an overall flame retarded composition for commercialSignificant increase in fife retardancy as application. All of theseASTM Tests are to be considmeasured by 0.1. (While these formulationsalso had a d as i t d h r in b reference. SB rating, 94, the individualrating has a The results of these tests show that the range of Valuesand thus the humbe in this Case, cal properties of the present inventioncompositions more indicative of increased flame ylare basically the same(except CI and UL 94 values) The use of an enhancing agent Such as z sto as the plastic material without the flame retardant (i.e. mote acooperative effect between Such agent and the formulation No; 1). Thus,there is no substantial ady y Compound fully demonstrated Via the verseeffect on the physical properties of the plastic sults obtained fromtestmg formulation Nos. 3, 5, 7, 9, material when the novel compoundsare incorporated 11, 13, 15, 17, 19, 21, 23, 25 and 26. The highest ULtherein 94 ratings and significantly higher, 0.]. values (9.512.0%increase) are obtained. EXAMPLE IV The procedure of Examples I and IIare repeated ex- EXAMPLE n cept that the enhancing agent used in zincborate in- Example 1 is repeated twice; once using a 10% bisstead of SbO Substantially the same results are obaryloxy compound level and 3% SbO level and setained using zinc borate as those obtained using Sb Ocondly, 20% and 10% levels respectively. At the 10%/3% level, the O.I.values and UL 94 ratings are EXAMPLE V slightly lower than the l5%/5%level of Example I. At Strip samples of each of Formulation Nos. 1through the 20%/l0% levels, the 0.1. values and UL 94 ratings areslightly higher but basically the same as those obtained using thel5%/5% level.

resultant plastic composition:

26 Table II, are subjected to light stability tests via the use of aWeather-Ometer, model 25/18 W. R., Atlas 1' ing an operating temperature;of 145 F and a 50% relative humidity, each strip is subjected to 200hours of simulated daylight via .theuse of a carbon, arc The resultsshow that after 20(;) hours, there is. no significant discoloration inany strip tested and which demonstrates that the present inventioncompositors are highly resistant to deterioration by light.

EXAMPLE Vl Samples of each of Formulation Nos. 1 through 26 Table II,are subjected to temperature (thermal) stability tests via the use ofthermal gravimet ric analysis (TGA). This test employed the use of aThermal Balance, model TGS-l, Perkin-Elmer Corporation, Norwalk,Connecticut and an electrical balance, Cahn 2580 model, Cahn InstrumentCompany, Paramount, California. The results of these tests show that thebisaryloxy compounds containing Formulations had more than adequatestability for melt processingand subsequent heat aging (i.e. hightemperature applications) and thus demonstrating that the particularfbis-aryloxy compounds are quite compatible with the plastic material.The bis-aryloxy compound stability thus aids in providing sufficientflame retardancy at the plastic decomposition temperature. This testalso demonstrates that these compounds do not exhibit migration.

ln view of the foregoing Examples and remarks, itis seen that theplastic compositions, which incorporate these compounds, possesscharacteristics which have been unobtainable in the prior art. Thus. theuse of these compounds in the above described plastic material as flameretardants therefor is quite unique since it is not possible to predictthe effectiveness and functionality of any particular material in anypolymer system until it is actively undergone incorporation therein andthe resultant plastic composition tested according to various ASTMStandards. Furthermore, it is necessary,

in order to have commercial utility, that the resultant flame retardedplastic composition possesscharacteris-' tics such as being non-toxic.Use of, these compounds in the plastic material has accomplished all ofthese objectives.

The above examples have been described in the foregoing specificationfor the purpose of illustration and not limitation. Many othermodifications and ramifications will naturally suggest themselves tothose skilled in the art based on this disclosure. These are intended tobe comprehended as within the scope of this invention. r I

. What is claimed is:

1. A plastic composition containing acrylonitrilebutadiene-styrenepolymer'having incorporated. therein a flame retardant which is abis-aryloxy compound having the formula:

wherein aryl is from the group alkylene is C H Z is selected from thegroup consisting of bromine or chlorine; m and hi. are integers 'havinga value of 1-7; y is an integer having a value of 1-5; i and i areintegers having a value of O'2; A is selected from the group consistingofcyano, .nitro, lower alkoxy, lower alkyl, fluorine,'dialkylamino.phenyl, halophenyl, benzyl or halobenzyl; and alklylene is a straight orbranched chain alkylene group having from 1 to 6 carbon atoms.

2. The composition as set forth in claim 1 wherein alkylene is C H 3.The composition as set forth in claim 1 wherein alkylene is C H 4. Thecomposition as set forth in claim 1 wherein alkylene is C H j 5. Thecomposition as set forth in claim 2 wherein Z is bromine. I

6. The composition as set forth in claim 2 wherein Z is chlorine.

7. A plastic composition containing acrylonitrilebutadiene-styrenehaving incorporated therein a flame retardant which is a bis-aryloxycompound having the formula:

Z is selected from chlorine; m is an integer having a value of F7; y isan, integer having a value of 1-5; 1' and i are integers-having a valueof 0-2; A is selected from the group consist.-

ing of cyano, nitro, lower alkoxy, lower alkyLfluorine, dialkylamino,phenyl, halo-phenyl, benzyl or halo-- kyleneis C- H 1 9. The compositionas set-forth-in claim 7 wherein alkylene is C H 1 Y I 10. Thecomposition as set forth in claim 7-wherein 11. The composition as setforth in'claim 8 wherein Z is bromine.

12. The composition as set forth in claim 8 wherein Z is chlorine. i f

13. A plastic composition containing acrylonitrilebutadiene-styrenehaving incorporated therein a flame retardant which is a bis-aryl oxycompound having the formula: 1 i

0 -(a1kylene)-OL/ y the group consisting of-bromine. or,

15. The composition as set forth in claim 13 wherein alkylene is C H 16.The composition as set forth in claim 13 wherein alkylene is C H 17. Thecomposition as set forth in claim 14 wherein Z is bromine.

18. The composition as set forth in claim 14 wherein Z is chlorine.

1. A PLASTIC COMPOSITION CONTAINING ACRYLONITRILE-BUTADIENESTYRENEPOLYMER HAVING INCORPORATED THEREIN A FLAME RETARDANT WHICH IS ABIS-ARYLOXY COMPOUND HAVING THE FORMULA:
 2. The composition as set forthin claim 1 wherein alkylene is C2H4.
 3. The composition as set forth inclaim 1 wherein alkylene is C3H6.
 4. The composition as set forth inclaim 1 wherein alkylene is C4H8.
 5. The composition as set forth inclaim 2 wherein Z is bromine.
 6. The composition as set forth in claim 2wherein Z is chlorine.
 7. A plastic composition containingacrylonitrile-butadiene-styrene having incorporated therein a flameretardant which is a bis-aryloxy compound having the formula:
 8. Thecomposition as set forth in claim 7 wherein alkylene is C2H4.
 9. Thecomposition as set forth in claim 7 wherein alkylene is C3H6.
 10. Thecomposition as set forth in claim 7 wherein alkylene is C4H8.
 11. Thecomposition as set forth in claim 8 wherein Z is bromine.
 12. Thecomposition as set forth in claim 8 wherein Z is chlorine.
 13. A plasticcomposition containing acrylonitrile-butadiene-styrene havingincorporated therein a flame retardant which is a bis-aryloxy compoundhaving the formula:
 14. The composition as set forth in claim 13 whereinalkylene is C2H4.
 15. The composition as set forth in claim 13 whereinalkylene is C3H6.
 16. The composition as set forth in claim 13 whereinalkylene is C4H8.
 17. The composition as set forth in claim 14 wherein Zis bromine.
 18. The composition as set forth in claim 14 wherein Z ischlorine.